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In Isaiah 14:29-32 we are given a short prophecy about Philistia, the land of the Philistines. The KJV calls it Palestina, because the name Palestine is derived from Philistia and was later applied to the land of Israel as well.
If we apply the previous verse (Isaiah 14:28) to this prophecy, then the prophet received this revelation in the year that King Ahaz died. The prophecy, then, would have reference to the events that had occurred during the latter part of Ahaz’ reign. Therefore, to understand what Isaiah was saying depends upon our knowledge of the events that had recently occurred.
But first we must go back two generations to Ahaz’ grandfather, Uzziah, and his conquest of Philistine cities.
Uzziah Conquers Philistine Cities
In 2 Chronicles 26:6 we read of the exploits of King Uzziah of Judah,
6 Now he went out and warred against the Philistines and broke down the wall of Gath and the wall of Jabneh and the wall of Ashdod; and he built cities in the area of Ashdod and among the Philistines.
We see, then, that there were Judahite communities (or colonies) in the area of Ashdod, which was a city near the coast of the Mediterranean Sea. Uzziah’s grandson, Ahaz, was an idolatrous king of Judah, and for this reason God caused Israel and Syria to form an alliance and to attack Judah. King Ahaz of Judah then appealed to Assyria for help, and Assyria’s intervention turned aside the attack on Judah.
When 120,000 Judahites were killed in just one battle (2 Chronicles 28:6), the Edomites and the Philistines each took advantage of the situation. So we read in 2 Chronicles 28:16-18,
16 At that time King Ahaz sent to the kings of Assyria for help. 17 For again the Edomites had come and attacked Judah and carried away captives. 18 The Philistines also had invaded the cities of the lowland and of the Negev of Judah and had taken Beth-shemesh, Aijalon, Gederoth, and Soco with its villages, Timnah with its villages, and Gimzo with its villages, and they settled there.
The reason God allowed Judah to be afflicted in this way was because Ahaz had “sacrificed to the gods of Damascus which had defeated him” (2 Chronicles 28:23) and “in every city of Judah he made high places to burn incense to other gods” (2 Chronicles 28:25). In other words, divine judgment came upon Judah, and for this reason, many men were killed or taken captive, and a number of cities were taken by the Philistines.
These events took place in the final years of the reign of King Ahaz, who died in 727 B.C. Isaiah then received his prophecy about Philistia (Isaiah 14:28). The prophecy was fulfilled about 15 years later. During the interim, the Assyrians took the Philistine cities and installed a puppet king in Ashdod named Ahimiti. Assyria remained allied with Judah during that time, and for this reason, Judah was not attacked until 713, or eight years after the fall of Samaria.
But the Philistines soon revolted against their puppet king and set up their own king named Yamani. The Assyrians then returned and invaded Philistia, forcing Yamani to flee. We read in Isaiah 20:1,
1 In the year that the commander [“Tartan”] came to Ashdod, when Sargon the king of Assyria sent him and he fought against Ashdod and captured it…
At that time the Assyrians decided to void their alliance with Judah and began capturing the cities of Judah as well. Isaiah attributes the Ashdod war to Sargon, who was the king of Assyria from 721-705 B.C. (His predecessor, Shalmanezer V, had invaded Israel and had captured Samaria. Not much is known about him, but it appears that he was killed and Sargon took the throne.) Eight years later, Sargon sent his commander (“Tartan”) to retake Ashdod, while his son Sennacherib invaded Judah. 2 Kings 18:13 calls Sennacherib the “king of Assyria,” so he was probably the co-regent with his father, as was the common practice in those days.
The invasion of Philistia was part of the campaign against Judah, where 46 walled cities of Judah were captured and its citizens deported to Assyria. Only then did they surround Jerusalem. Recall that God then destroyed 185,000 Assyrian troops, which ended the war.
With this background, let us look at Isaiah’s prophecy to Philistia.
Do Not Rejoice
Assuming that this prophecy came in the year that Ahaz died (Isaiah 14:28), we note that it came to pass 15 years later. Isaiah 14:29 begins,
29 Do not rejoice, O Philistia, all of you, because the rod that struck you is broken; for from the serpent’s [nachash] root a viper [tsephah] will come out, and its fruit will be a flying serpent [seraph].
It tells the Philistines not to rejoice that “the rod that struck you is broken.” There is some question as to who was “the rod.” Obviously, it was the rod of God, because God always took credit for what His agents did. The rod may have been Judah, which had occupied Ashdod in the days of Uzziah, or it may have been the later “rod” of Assyria.
Either way, the Philistines were not to rejoice when they saw the Assyrian army destroying Judah, because the Philistines were not going to be set free of occupation. They were only to change masters. If “the rod” was a reference to Assyria, then Isaiah 14:29 prophesies the destruction of the Assyrian army, which ended its occupation in the entire region.
In other words, the prophecy instructs the Philistines not to “rejoice” over its escape from conquest and occupation.
The Serpent’s Root
Isaiah tells Philistia that “from the serpent’s root a viper will come out, and its fruit will be a flying serpent.” The first “serpent” (with the “root”) is the Hebrew word nachash, the same word used of the original tempter in the Garden (Genesis 3:1). The “flying serpent” is the same as “the fleeing serpent” in Isaiah 27:1, also known as “Leviathan.”
The “root” of the serpent, in this case, is the underlying cause, or the “father,” even as Jesse was the “root” of David in Isaiah 11:1. This root produces offspring, “and its fruit will be a flying serpent,” that is, a serpent that is fleeing or trying to flee.
In the prophecies of the constellations, the fleeing serpent (Serpens) is pictured as a serpent trying to escape from Ophiuchus, the “Serpent-Holder.” Ophiuchus is an early picture of Christ in His role as the great Healer. Greek mythology called him Aesculapius, who was the god of healing. Unfortunately, they perverted the truth and thus introduced the worship of false gods, including the false god of healing.
Serpens is pictured attempting to seize the crown (“Corona”), but Ophiuchus prevents him from achieving his goal. So also the serpent (the devil) attempts unsuccessfully to usurp the crown that belongs to Christ.
Isaiah’s prophetic metaphor tells Philistia that it can neither take the crown (as a free country) nor can it escape the dominion of Christ. For this reason, Philistia should not rejoice when it appears that they might be able to regain their freedom from either Judah or Assyria.